Shipping, regardless the sellers feedback, or packing, is a coin toss at best. Many dealers Ive spoken with have said that their major obstacle in selling is the carrier.
Despite the horror stories surrounding shippers, the majority of shipped items arrive safely. Carriers couldn't stay in business if they didn't.
However, it's my major concern when buying outside of my locale.
If there's no original packing then I'll usually pass on the deal. Or I'd ask the seller to have the shipper for the whatever thing, do their own packing process. The latter is no slam dunk on a safe arrival, but a far better way to wind up with a easier path for recovery from the packer - carrier.
Even if it is all orig, but has changed hands several times and isnt in great shape as the result of all those frequently traveled miles, Id be double sure to cover the quality of the container with the seller up front. New containers can be had from the orig maker . IF its not to dated a component. The fee for this can be at first a pricey aspect added onto the purchase, but a true benefit to the then buyer, and perhaps to the next as well.
If it has been packed well and is an expensive item, say over 2 grand, then Id add a couple hundred +/- to overnight the item to you. Also, air is no guarantee of safe delivery, but it is handled a few less times.
I have bought and sold speakers to and from one coast to the other. All in their orig packing without damages to the speakers themselves. The packing however in some cases did not fare quite so well but then thats the job of the packing. Right?
The insurance aspect? Its not really insurance, but merely a declared value which HAS to be supported by affidavits such as a bill of sale receipts invoices etc., in thje event of any claim. Perhaps all of the above too. Spend as much as you wish to cover an item being sold or bought. In the end however, if some claim is sought, only the supported actual loss can be recovered.
Along with the bill of sale you can ask for a statement from the seller which allows you to initiate, continue, and settle a claim. Carriers, by and large, see the point of origin as the shipper and wish to deal only with them for purposes of possible claims... regardless who has actually paid for the shipping!
No item is entirely safe from mishandling. None. Lighter things seem to be less risky than heavy things, or large things . BUT it seems to me to come down to this one item ....
is your prospective purchase worth taking the risk of shipping to have it?
Id venture a guess that many here will agree it is IF all the other C.Y.A. bases listed herein are covered.